Cannabis Compound Database: Showing Compound Card for Formic acid (CDB000608)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (12) Show 40 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:46:25 UTC

Updated at

2020-12-07 19:07:34 UTC

CannabisDB ID

CDB000608

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Formic acid

Description

Formic acid, also known as methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts, and the anion derived from formic acid are called formates. Industrially, formic acid is produced through the oxidation of methanol. Formate is an intermediate in normal metabolism. It takes part in the metabolism of one-carbon compounds and its carbon may appear in methyl groups undergoing transmethylation. It is eventually oxidized to carbon dioxide. Formate is typically produced as a by-product in the production of acetate. It is responsible for both metabolic acidosis and disrupting mitochondrial electron transport and energy production by inhibiting cytochrome oxidase activity, the terminal electron acceptor of the electron transport chain. Cell death from cytochrome oxidase inhibition by formate is believed to result partly from depletion of ATP, reducing energy concentrations so that essential cell functions cannot be maintained. Furthermore, inhibition of cytochrome oxidase by formate may also cause cell death by increased production of cytotoxic reactive oxygen species (ROS) secondary to the blockade of the electron transport chain. In nature, formic acid is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer. Urinary formate is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis, Streptococcus group B, Staphylococcus saprophyticus (PMID: 22292465 ). Formic acid has also been detected as a volatile component in cannabis plant samples (PMID: 26657499 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acide formique	ChEBI
Ameisensaeure	ChEBI
Aminic acid	ChEBI
Bilorin	ChEBI
Formylic acid	ChEBI
H-COOH	ChEBI
HCO2H	ChEBI
HCOOH	ChEBI
Hydrogen carboxylic acid	ChEBI
Methanoic acid	ChEBI
Methoic acid	ChEBI
Aminate	Generator
Formylate	Generator
Hydrogen carboxylate	Generator
Methanoate	Generator
Methoate	Generator
Formate	Generator
Add-F	HMDB
Ameisensaure	HMDB
Collo-bueglatt	HMDB
Collo-didax	HMDB
Formira	HMDB
Formisoton	HMDB
Methanoic acid monomer	HMDB
Myrmicyl	HMDB
Sodium formate	HMDB
Sybest	HMDB
Wonderbond hardener m 600l	HMDB
Calcium formate	HMDB
Cobalt(II) formate dihydrate	HMDB
Formic acid, aluminum salt	HMDB
Formic acid, copper salt	HMDB
Formic acid, cromium (+3) salt	HMDB
Lithium formate	HMDB
Ammonium formate	HMDB
Formic acid, ammonium (4:1) salt	HMDB
Formic acid, ammonium salt	HMDB
Formic acid, calcium salt	HMDB
Formic acid, copper (+2) salt	HMDB
Formic acid, lead (+2) salt	HMDB
Formic acid, lead salt	HMDB
Formic acid, nickel salt	HMDB
Formic acid, potassium salt	HMDB
Formic acid, strontium salt	HMDB
Mafusol	HMDB
Ammonium tetraformate	HMDB
Formic acid, 14C-labeled	HMDB
Formic acid, cobalt (+2) salt	HMDB
Formic acid, copper, ammonium salt	HMDB
Formic acid, sodium salt	HMDB
Formic acid, sodium salt, 14C-labeled	HMDB
Formic acid, ammonium (2:1) salt	HMDB
Formic acid, cadmium salt	HMDB
Formic acid, cesium salt	HMDB
Formic acid, copper, nickel salt	HMDB
Formic acid, cromium (+3), sodium (4:1:1) salt	HMDB
Formic acid, lithium salt	HMDB
Formic acid, magnesium salt	HMDB
Formic acid, nickel (+2) salt	HMDB
Formic acid, rubidium salt	HMDB
Formic acid, sodium salt, 13C-labeled	HMDB
Formic acid, thallium (+1) salt	HMDB
Formic acid, zinc salt	HMDB
Nickel formate dihydrate	HMDB
Aluminum formate	HMDB
Potassium formate	HMDB
Strontium formate	HMDB
Lead formate	HMDB
Nickel formate	HMDB
Chromic formate	HMDB
Cobaltous formate	HMDB
Cupric formate	HMDB
Magnesium formate	HMDB
Zinc formate	HMDB

Chemical Formula

CH₂O₂

Average Molecular Weight

46.03

Monoisotopic Molecular Weight

46.0055

IUPAC Name

formic acid

Traditional Name

formic acid

CAS Registry Number

64-18-6

SMILES

OC=O

InChI Identifier

InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)

InChI Key

BDAGIHXWWSANSR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic acids

Alternative Parents

Substituents

Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:30751 )
Straight chain fatty acids (C00058 )
Saturated fatty acids (C00058 )

Ontology

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Environmental contaminant

Industrial application:

Drug

Household products:

Antimicrobial agent:

Antibacterial

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	8.4 °C	Not Available
Boiling Point	100.8 °C	Wikipedia
Water Solubility	1000 mg/mL	Not Available
logP	-0.54	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-0.47	ALOGPS
logP	-0.27	ChemAxon
logS	1.02	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	8.15 m³·mol⁻¹	ChemAxon
Polarizability	3.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-004j-9000000000-2e63b0c1e2e417b0d747	2015-03-01	View Spectrum
Predicted GC-MS	Formic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9000000000-5d27bb312e37a2c8994f	Spectrum
Predicted GC-MS	Formic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fmi-9200000000-2a89ba98485194acd75a	Spectrum
Predicted GC-MS	Formic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Formic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-0002-9000000000-a8fbddf8ca4197b30013	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 5V, positive	splash10-0002-9000000000-98310116f8a2d6a969ce	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 6V, positive	splash10-0002-9000000000-ec8753fd9790a3cf0be8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 7V, positive	splash10-0002-9000000000-121d1a025b72a70e412a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-0002-9000000000-5f1955dee7ab988e86dd	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 9V, positive	splash10-0002-9000000000-f8e14272296ee06d19f4	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-092f816e62c8d2f5d56e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-092f816e62c8d2f5d56e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-092f816e62c8d2f5d56e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-eb2207f7400e9144fff7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-eb2207f7400e9144fff7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-eb2207f7400e9144fff7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-d948d5d95ae14e701f57	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-d948d5d95ae14e701f57	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d948d5d95ae14e701f57	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-92190863fc6ae28a8789	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-92190863fc6ae28a8789	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-348f481062f48991a0aa	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Pterine Biosynthesis
Folate Metabolism
Methotrexate Action Pathway		Not Available
Folate malabsorption, hereditary		Not Available
Steroid Biosynthesis

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Lanosterol 14-alpha demethylase	CYP51A1	7q21.2	Q16850	details
S-formylglutathione hydrolase	ESD	13q14.1-q14.2	P10768	details
Aspartoacylase	ASPA	17p13.3	P45381	details
Aspartoacylase-2	ACY3		Q96HD9	details
C-1-tetrahydrofolate synthase, cytoplasmic	MTHFD1	14q24	P11586	details
GTP cyclohydrolase 1	GCH1	14q22.1-q22.2	P30793	details
Peptide deformylase, mitochondrial	PDF	16q22.1	Q9HBH1	details
Monofunctional C1-tetrahydrofolate synthase, mitochondrial	MTHFD1L	6q25.1	Q6UB35	details
Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolase	MTHFD2	2p13.1	Q7Z650	details
Kynurenine formamidase	AFMID	17q25.3	Q63HM1	details
Cytochrome P450, family 1, subfamily A, polypeptide 1	CYP1A1	15q24.1	A0N0X8	details
1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenase	ADI1	2p25.3	Q9BV57	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Lanosterol 14-alpha demethylase	CYP51A1	7q21.2	Q16850	details
Aspartoacylase	ASPA	17p13.3	P45381	details
Aspartoacylase-2	ACY3		Q96HD9	details
Cytochrome P450 3A4	CYP3A4	7q21.1	P08684	details
Cytochrome P450 2C9	CYP2C9	10q24	P11712	details
Cytochrome P450 2C19	CYP2C19	10q24	P33261	details
Peptide deformylase, mitochondrial	PDF	16q22.1	Q9HBH1	details
Cytochrome P450 2E1	CYP2E1	10q24.3-qter	P05181	details
Cytochrome P450 3A43	CYP3A43	7q21.1	Q9HB55	details
Cytochrome P450 1B1	CYP1B1	2p22.2	Q16678	details
Cytochrome P450 2C18	CYP2C18	10q24	P33260	details
Cytochrome P450 2F1	CYP2F1	19q13.2	P24903	details
Cytochrome P450 4X1	CYP4X1	1	Q8N118	details
Cytochrome P450 2B6	CYP2B6	19q13.2	P20813	details
Cytochrome P450 3A5	CYP3A5	7q21.1	P20815	details
Cytochrome P450 2A13	CYP2A13	19q13.2	Q16696	details
Cytochrome P450 3A7	CYP3A7	7q21-q22.1	P24462	details
Cytochrome P450 4B1	CYP4B1	1p34-p12	P13584	details
Cytochrome P450 4Z1	CYP4Z1	1p33	Q86W10	details
Cytochrome P450 1A2	CYP1A2	15q24.1	P05177	details
Cytochrome P450 19A1	CYP19A1	15q21.1	P11511	details
Cytochrome P450 2C8	CYP2C8	10q23.33	P10632	details
Cytochrome P450 2S1	CYP2S1	19q13.1	Q96SQ9	details
Cytochrome P450 2J2	CYP2J2	1p31.3-p31.2	P51589	details
Cytochrome P450 2A7	CYP2A7	19q13.2	P20853	details
Cytochrome P450 2A6	CYP2A6	19q13.2	P11509	details
Cytochrome P450, family 1, subfamily A, polypeptide 1	CYP1A1	15q24.1	A0N0X8	details
1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenase	ADI1	2p25.3	Q9BV57	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000142

DrugBank ID

DB01942

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012804

KNApSAcK ID

C00001182

Chemspider ID

Not Available

KEGG Compound ID

C00058

BioCyc ID

FORMATE

BiGG ID

Not Available

Wikipedia Link

Formic_acid

METLIN ID

Not Available

PubChem Compound

284

PDB ID

Not Available

ChEBI ID

30751

References

General References

Gupta A, Dwivedi M, Mahdi AA, Khetrapal CL, Bhandari M: Broad identification of bacterial type in urinary tract infection using (1)h NMR spectroscopy. J Proteome Res. 2012 Mar 2;11(3):1844-54. doi: 10.1021/pr2010692. Epub 2012 Jan 31. [PubMed:22292465 ]
Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Only showing the first 10 proteins. There are 40 proteins in total.

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Enzymes

Enzyme Details

1. Lanosterol 14-alpha demethylase

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:: CYP51A1
Uniprot ID:: Q16850
Molecular weight:: 57277.81

Enzyme Details

2. S-formylglutathione hydrolase

General function:: Involved in carboxylesterase activity
Specific function:: Serine hydrolase involved in the detoxification of formaldehyde.
Gene Name:: ESD
Uniprot ID:: P10768
Molecular weight:: 31462.545

Enzyme Details

3. Aspartoacylase

General function:: Involved in hydrolase activity, acting on ester bonds
Specific function:: Catalyzes the deacetylation of N-acetylaspartic acid (NAA) to produce acetate and L-aspartate. NAA occurs in high concentration in brain and its hydrolysis NAA plays a significant part in the maintenance of intact white matter. In other tissues it act as a scavenger of NAA from body fluids.
Gene Name:: ASPA
Uniprot ID:: P45381
Molecular weight:: 35734.79

Enzyme Details

4. Aspartoacylase-2

General function:: Involved in hydrolase activity, acting on ester bonds
Specific function:: Plays an important role in deacetylating mercapturic acids in kidney proximal tubules (By similarity).
Gene Name:: ACY3
Uniprot ID:: Q96HD9
Molecular weight:: Not Available

Enzyme Details

5. C-1-tetrahydrofolate synthase, cytoplasmic

General function:: Involved in formate-tetrahydrofolate ligase activity
Specific function:: Not Available
Gene Name:: MTHFD1
Uniprot ID:: P11586
Molecular weight:: 101530.36

Enzyme Details

6. GTP cyclohydrolase 1

General function:: Involved in GTP cyclohydrolase I activity
Specific function:: Positively regulates nitric oxide synthesis in umbilical vein endothelial cells (HUVECs). May be involved in dopamine synthesis. May modify pain sensitivity and persistence. Isoform GCH-1 is the functional enzyme, the potential function of the enzymatically inactive isoforms remains unknown.
Gene Name:: GCH1
Uniprot ID:: P30793
Molecular weight:: 27902.855

Enzyme Details

7. Peptide deformylase, mitochondrial

General function:: Involved in iron ion binding
Specific function:: Removes the formyl group from the N-terminal Met of newly synthesized proteins (By similarity).
Gene Name:: PDF
Uniprot ID:: Q9HBH1
Molecular weight:: 27013.25

Enzyme Details

8. Monofunctional C1-tetrahydrofolate synthase, mitochondrial

General function:: Involved in formate-tetrahydrofolate ligase activity
Specific function:: May provide the missing metabolic reaction required to link the mitochondria and the cytoplasm in the mammalian model of one-carbon folate metabolism in embryonic an transformed cells complementing thus the enzymatic activities of MTHFD2 (By similarity).
Gene Name:: MTHFD1L
Uniprot ID:: Q6UB35
Molecular weight:: 105888.19

Enzyme Details

9. Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: MTHFD2
Uniprot ID:: Q7Z650
Molecular weight:: 26849.1

Enzyme Details

10. Kynurenine formamidase

General function:: Involved in hydrolase activity
Specific function:: Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites (By similarity).
Gene Name:: AFMID
Uniprot ID:: Q63HM1
Molecular weight:: 33991.5

Only showing the first 10 proteins. There are 40 proteins in total.

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Showing Compound Card for Formic acid (CDB000608)

Structure for CDB000608 (Formic acid)

Enzymes